The resolved 1,2,3,4-tetrahydro-1-naphthylamines have been reported in the literature by R. Weidmann and J. P. Guette, Comptes Rendus des Seances de l'Academie des Sciences 268:2225 (1969) as resulting from the Curtius reactions with optionally active 1,2,3,4-tetrahydronaphthalene1-carboxylic acid azides. This work establishes the absolute configuration of the (R) and (S) isomers, but does not suggest the 1,2,3,4-tetrahydro-4-oxo(oxy)-1-naphthylamines of the present invention, nor does it suggest the 1,2,3,4-tetrahydro-4-oxo(oxy)-1-naphthylureas or thioureas derived therefrom. The above urea and thiourea compounds are described and claimed in my application for U.S. letters patent Ser. No. 582,559, filed May 30, 1975, now abandoned.
Further, the above-referred-to article does not suggest the 1,2,3,4-tetrahydro-4-oxo(oxy)-1-naphthylisocyanates or isothiocyanates derived from the novel tetrahydro-4-oxo(oxy)-1-naphthylamines of the present invention. The above isocyanates and isothiocyanates are described and claimed in my application for U.S. letters patent Ser. No. 628,030, filed Nov. 3, 1975, now Patent No. 3,993,677. Both applications are incorporated herein by way of reference.
This invention also relates to methods of preparation of the above-identified 1,2,3,4-tetrahydro-4-oxo(oxy)-1-naphthylamines.